Acetic Anhydride → HCID 68587171, compound

HRID 1808720Notes

Reaction equation

HRID 1808720 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH3:20])[CH2:9][CH:8]([OH:10])[O:7][CH:6]1[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:4].[C:21](OC(=O)C)(=[O:23])[CH3:22]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1([CH3:20])[CH2:9][CH:8]([O:10][C:21](=[O:23])[CH3:22])[O:7][CH:6]1[CH2:11][O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:4]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 68587353HCID 68587353, compound

Product 1

HCID 68587171HCID 68587171, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-Benzyloxymethyl-5-hydroxy-3-methyl-tetrahydro-furan-3-carboxylic acid methyl ester (0.48 g, 1.7 mmol) prepared as previously described, in pyridine (5 mL), Acetic Anhydride (0.32 mL, 3.4 mmol) and DMAP (5 mg) were added and the reaction was stirred at room temperature. After 3 h stirring, the reaction mixture was diluted with ethyl acetate, washed with 0.5N HCl and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue obtained was purified by column chromatography (EA/Hexanes, 40:60). The product was isolated as a 2.8/1 anomeric mixture.

Workup

  1. stirringAfter 3 h stirring
  2. washwashed with 0.5N HCl and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98c5f6d47698414b8d2f37a86ab671bc
Source dataset
uspto-grants-2013_01
Patent number
US08361988B2

Reaction notes

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